Friends With Kids
by fox24
Summary: Rory and Logan are both best friends and single parents with kids struggling to find love in the big city. AU
1. Chapter 1

_I had a new and original idea about a AU dynamic in RL's relationship and I wanted to explore that. If you think I should continue please tell me. _

Rory Gilmore got back into her large New York apartment. It was hard to believe she was living here after the dump she shared with Jess almost ten years ago. At 19 she had made a out of character decision, she had run off with Jess. At first it had been an adventure, but then she had gotten pregnant and Jess had left her not wanting the responsibility of raising a child.

Jess had come around five years later wanting Rory and his daughter to be a part of her life. Rory refused to get back together with Jess but gave their daughter visiting weekends with the promise he wouldn't bail on the daughter. Jess to his credit had kept that promise and treated their daughter well. Although Jess seemed to only do it to fulfill his duty than wanting to be a loving father.

Rory had no choice but to turn to her grandparents. To their credit they acted better than they did when Lorelai had gotten pregnant. They had not lectured her on ruining her reputation or forced to track down Jess and marry him. They had agreed to let Rory and the baby live in their Pool house. The only conditions were for Rory to finish Yale and to let them pay for housing after the baby was born. Rory found those conditions fair and her grandparents had been a big help to her and her daughter Riley Lorelai Gilmore was born. Rory was able to finish school and secure a job at a Huntzburger paper in New York. Her grandparents had found her a beautiful apartment in New York and helped pay for Riley's schooling.

While Rory's relationship with her grandparents had improved her relationship Lorelai had deteriorated. Lorelai did not like that Rory went to her grandparents and not her, when she had gotten pregnant. She seem to be constantly passive aggressive about that fact and even though she was a good grandmother to Riley, she always seem to put Rory's choices and parenting skills down saying Rory was spoiling Riley and should move to SH and not NY. The only times Lorelai seemed to lay off was when Rory dated a guy she approved, which was when she dated Marty for 2 years and her recent boyfriend James. Unfortunately, for Rory she and James had just broken up because he couldn't handle raising a child, if things with Rory got more serious.

Rory tried to be grateful for the relationships she had. She still had her father, Paris, Lane, Honor, Colin, Finn and Logan. Logan was her best friend ever since she moved to New York after college at 23. He was her boss at the paper and her next door neighbor. He also had a daughter from a one night stand who was close to Riley's age Jenna. Jenna and Riley were inseparable. Logan had baby sited often for Riley and Riley adored him. Rory also adored Jenna, who had her father's energy but yet a serious side as well.

Logan had been there for Rory through her break up with Marty, fights with Lorelai, when Riley first spend the night at Jess's, and she had been there for him as well through work crisis, and his own tense relationship with his father.

Rory wished Logan was here for her now. However, he was on a date with a girl he taken a fancy to at the coffee shop. Rory did not why she felt a knot in her stomach at the thought of that she was happy that the girl seemed nice. She figured she was just lonely after her break up, she had spend a day doing retail and beauty therapy by buying several new outfits, getting her hair done, and getting a mani-pedi. She figured a good book would distract her. She started to read the same sentence three times, when she suddenly heard the door ring. She was surprised to see Logan carrying two boxes of food. "Hey what are you doing here, I thought you had a date.

Rory followed Logan to the couch in the living room. Logan handed the two boxes of food to her and Rory set them on the table in front of the sofa. "I just felt funny leaving you at home alone, plus I felt a little scared that you were going to the beauty parlor. Logan glanced at her and breathed a sigh of relief. Thank god, you just got a trim and didn't chop off your hair this time. " Logan said referring to her last break up with Marty two years, where she had cut her rich long locks to the nap of her neck.

"Wow you noticed my trim, seriously, with Marty, Jess, and James I go come in bald and they wouldn't even notice. Plus the short hair cut wasn't that bad…" Although Rory had no desire to cut her hair that short again, she looked pretty childish in photos.

"No you look like a cute 12 year old…" Logan joked. He always found Rory to be pretty but really short hair just was not her.

"Very funny Logan. I saw the picture of your shaved head from Honor's album, when you were 16 were you going to for the 50 cent look."

He would kill his sister. "Hey that was for the summer and it did look cool. I think I might do that again…"

"I can't wait to see the look on Mitchum's face, when you do that. Maybe I should make another hair appointment to cut my hair that short again tomorrow after all I also thought it looked cool as well. "Rory teased hoping it would be one of those rare times, when Logan conceded to an argument.

"Okay you were right it was kind of dumb." He hated to concede to an argument but he didn't want Rory to sacrifice her beautiful hair just to prove a point.

"Nice to see you agree with me Logan. Did you really interrupt your date just to see if I didn't get an "I am sad I broke up with my boyfriend haircut." Rory gently patted him on the shoulder.

"Not just that I wanted to see if you were okay physically and emotionally. I see you look good physically…He said glancing at her trip to the salon had made her hair appear shiny and glowing. He didn't know why his heart skipped a beat, she was just his friend.

Rory did not know why his compliments had an effect on her." Thank you Logan. I am not money conscious but I am grateful my trust fund helps me get beauty treatments during my time of need. Emotionally, I just feel weird are guys going to find out about Riley and then run from the hills."

"Is that why the jerk broke up with you?" Logan asked almost mad.

"Sort of he didn't think he would make a good step father and it scared him. I guess I understand and it's good that he was honest with me, but it's still hard. I really thought he was good long term material and my mom liked him."

"Things are still tense between you and Lorelai." Logan knew that things were tense with her mother ever since she decided to run away with Jess and then later accept help from her grandparents from the baby.

"Yeah, I feel that if it wasn't for Riley we wouldn't be talking. When I was with James and Marty, she seemed to ease up on me because they didn't come from money and worked hard to make their living. I don't know what to do when I come home for William's baptism." William was the child Lorelai had with Luke.

"I'll come with you…" Logan offered.

"That's sweet Logan, but my hates you…" She was very frosty to Logan the few times she visited the apartment.

"I don't care, I don't want you to be miserable." Logan stated.

"Thanks, I owe you one. I'll be your date at the next gala Mitchum wants you to attend. Unless, your taking Cara."

"Oh that's over. Another reason why I caught the date early." Logan shuddered.

Rory opened the boxes of food there was lobster tail, crab cakes, and cheese cake. "Let me guess she didn't have a big appetite hence my five course dinner."

"Worse, I told her I had a 7 year old daughter and acted like if we ever got serious she'd send her to boarding school. She and my mom would get along perfectly."

"Yikes" While Mitchum adored his granddaughter, Shira not so much.

"So where's Jenna tonight?" Rory asked curiously.

"At Honor's they added a new Kareoke machine…" His daughter loved to sing.

"Sounds fun, Riley's at my Mom. Do you want to have some wine and cheer towards the drama of dating while you have a kid."

"Would gladly love to Ace."


	2. Secrets Revealed

**It's been awhile since I posted an update of this I needed to get back into the mindset of this story. Don't worry Jess won't be in this story for a while and I am not going to get into the details of Riley's conception. Plus Riley will have some of Logan's qualities and she won't be a matchmaker for Rory and Jess but Rory and Logan. **

"God remember when you pretended to be Smitty at the YDN." Rory smiled at the memory. She and Logan weren't exactly friends in college but she had such amusing memories of him coming into the Yale Daily News on the days he was obligated to submit an article.

"I knew I saw you smiling…" Logan smirked.

"No I wasn't I thought it was rude that you weren't taking the paper seriously and once in a blue moon you would write better articles better than I did. " It didn't bother her anymore Logan's writing made her think, make her laugh, and inspire her to write better.

"Hey you were a good writer back in college. I would actually read your stuff for fun. I especially loved what you wrote about the ballerina. " He remembered how he had spent an hour laughing at Rory's criticism of the performance.

"Logan that was a mean article the girl's show had to be canceled. " She still felt bad about that story.

"Sometimes you have to be honest Ace. Speaking of that why weren't we friends in college?"

Rory thought for a long moment before she answered. "Cause I was pregnant my sophomore year and didn't want anyone to know with the exception of close friends so wore a lot of ugly and baggie clothes. I would only go to class, newspaper, doctor's appointment and home. I then had a baby to take care and I didn't have time to go clubbing, bar hopping, and secret societies. We didn't really run into the same places."

"Yeah we didn't…" Logan thought sadly. Although he understood how busy a child could be, when he was given the shock of his life at the end of his senior year when a baby was dropped on his door step. He was lucky that Mitchum let him stay in New York instead of going to London to find out that Jenna was his and to learn how to be the father to Jenna that Mitchum never was to him.

"Do you ever get sad that you missed out on your college years?" He didn't know what he would if he didn't have those 4 years of partying and hanging out.

"Logan I was never Ms. Party Girl but I do sometimes wish I had more fun in High School and college. However, in a weird way I have more fun with you than I ever did as teenager" Rory smiled thinking of all the fun activities she and Logan had done.

"Ace you had a really sad adolescence. " Logan replied in jest.

"At least I wasn't a poor little rich boy." Rory teased back.

"Hey poor little rich boy is better than teacher's pet having a fling with the small town's hooligan." Logan was worried he had gone a little too far.

However, Rory fired back. "It's better than sleeping with a bunch of people that you don't remember a majority of their names. Although I guess you're going to fire back with teen pregnancy." Rory started to feel concern their banter went a little too far.

"Rory come I would never do that I love Riley and I had a kid two years later by some girl that all I knew about was her name was Monica. I love Jenna more than anything but it's not the way I pictured having a kid."

Rory softened. "I didn't picture having a kid like that either. I didn't picture telling my mom I was pregnant and her hanging up the phone."

Logan looked deep into Rory's eyes. "Is that what happened. I thought you said she holds resentment because you went to your grandparents instead of her"

Rory had never admitted that part to anyone and took a deep breath. "My mom has a very select memory on what happened. I called her first when Jess had left and she got angry and hang up. I then immediately called my grandparents and they immediately came up with a plan. A few hours later my mom called to apologize and got mad that I was going to follow my grandparents plan. I tried to explain my side but she is just so passive aggressive."

Logan couldn't believe Lorelai could be so childish. "Don't let her get to you, I mean you did what you thought was best. "

Rory was touched on how Logan could always find the right words to make her feel better. I know Logan. "She felt like she was going to cry she quickly needed a distraction. "Come on lets go watch a comedy this is turning into a melodrama."

"Good idea Ace." A part of him wished he could say and do more to comfort her but he was very happy that he was able to make her feel better.

Rory woke up feeling slightly disoriented; there was mysterious familiar warmth around her waist. She looked around the room it looked like her living room table filled with plates and wine glasses. She then remembered her and Logan having a long dinner and movie night. Did they fall asleep in front of a movie again?

She suddenly noticed that she was huddled next to a body with a familiar shade of blond hair. She couldn't help smiling when she saw that Logan had embraced her in his sleep. It tended to happen from time to time and Rory couldn't understand why she would feel a sense of elation whenever it tended to happen. She tried to brush the inappropriate thoughts she tended to have of Logan from time of time. Logan was one of the few stable people she had in her life and she did not want to lose him if a romantic relationship did not work out.

She tried to focus she looked at the clock it was around she needed to call her Mom to make sure Riley was okay. She struggled reluctantly to get out of Logan's strong grip around her waist. When she finally was able to let go, she quickly went and grabbed her cell phone from her purse and dialed her mother's phone number.

"Honey anything wrong it's late…." Lorelai asked in concern.

"No nothing like I just fell asleep and I forgot to check in with you about Riley." She didn't feel like sharing with her mom about her break up or hanging out with Logan.

Lorelai appeared to be unfazed and happy at the question. "She had a great time, she Martha, and another girl from the neighborhood played jump rope and hop scotch."

Rory smiled. "I have no idea where that girl gets her love of physical activity." She guessed it might have been a gene Christopher had that skipped a generation but then she thought of the time Logan played jump rope with her back in Central Park. Logan really did a lot for Riley. Rory tried to focus on the conversation at hand.

"You know she really does have friends if you ever think about moving back." Lorelai said in a hopeful tone.

Rory rolled her eyes Lorelai was so not good at being subtle. "Mom I am glad Riley has fun when she comes and visits you but we both have a life here, I do not want to uproot her. " Rory said hoping Lorelai could drop the subject.

"Of course sometimes I just worry your spoiling her. I mean she asked me what a mansion was."

Rory rolled her eyes. "Mom Honor read her the _Baby Sitters Club_ and the character Kristy moves into a mansion so she was a little curious about that and I make her do chores. I try to make sure she is not waited on hand and foot." Rory hated that she had to defend herself every time Riley would ask something about rich people or look too fancy to Lorelai. Rory tried her best with Riley and whatever she did it just wasn't enough for Lorelai.

"Okay." Lorelai said dropping the subject. "How's James?"

Rory groaned she wasn't ready to tell her telling Lorelai would mean more remarks of disapproval. "He's doing well Mom?"

"Well I am glad. He seemed to really love Stars Hollow when he visited maybe he can come this weekend?" Lorelai asked hopefully.

"James is busy this weekend maybe another time. What else did Riley do today?" Rory said eager to change the subject.

Lorelai continue to comment on Riley's day. At the end of the exhausting phone call Rory decided to have some water and go to bed.

She was surprised to see Logan right behind her. "You haven't told her yet…."

"I couldn't she'll get worse if she finds out that I broke up with a guy that she likes she's turned into my grandmother these past eight years."

Logan started to pat her back. "You're going to have to tell her. It's going to kill you keeping that big a secret from her."

"I know." Logan pulled her close and Rory leaned against him feeling her problems with Lorelai melt away and feeling the comfort of Logan's arms.


End file.
